Facile Synthesis of 1-Arylpyrazoles

Yiwen Yang; Chunxiang Kuang

doi:10.1055/s-0034-1380658

Synthesis, Table of Contents

Synthesis 2015; 47(15): 2281-2284
DOI: 10.1055/s-0034-1380658

paper

Facile Synthesis of 1-Arylpyrazoles

Yiwen Yang*

^aCollege of Biological, Chemical Sciences, and Engineering, Jiaxing University, Jiahang Road 118, Jiaxing 314001, P. R. of China Email: yangyiwen@mail.zjxu.edu.cn

,

Chunxiang Kuang*

^bDepartment of Chemistry, Tongji University, Siping Road 1239, Shanghai 200092, P. R. of China Email: kuangcx@tongji.edu.cn

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Abstract

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Abstract

A convenient and transition-metal-free synthesis of 1-arylpyrazoles that involves the cycloaddition of 3-arylsydnones and acrylic acid is presented. The process proceeds smoothly to obtain the target products with moderate to high yields.

Key words

pyrazoles - 1,3-dipolar cycloaddition - sydnones - acrylic acid - metal-free reactions

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References

References
1 Lien JC, Huang LJ, Wang JP, Teng CM, Lee KH, Kuo SC. Bioorg. Med. Chem. 1997; 5: 2111
2 Bekhit AA, Abdel-Aziem T. Bioorg. Med. Chem. 2004; 12: 1935
3 Ryu CK, Song EH, Shim JY, You HJ, Choi KU, Choi IH, Lee EY, Chae MJ. Bioorg. Med. Chem. Lett. 2003; 13: 17
4 Vishnu KT, Dharmendra BY, Ashok KC, Praveen KS. Bioorg. Med. Chem. Lett. 2005; 15: 3288
5 Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954

6a Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS, Anderson GD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY, Isakson PC. J. Med. Chem. 1997; 40: 1347
6b Kujubu DA, Fletcher BS, Varnum BC, Lim RW, Herschman HR. J. Biol. Chem. 1991; 266: 12866

7 Sun X, Tian J, Zhu M, Chai B, Liu C. Agrochemicals 2011; 50: 781

8a Taillefer M, Xia N, Ouali A. Angew. Chem. Int. Ed. 2007; 46: 934
8b Correa A, Bolma C. Adv. Synth. Catal. 2007; 349: 2673
8c Chen W, Zhang Y, Zhu L, Lan J, Xie R, You J. J. Am. Chem. Soc. 2007; 129: 13879
8d Suresh P, Pitchumani K. J. Org. Chem. 2008; 73: 9121
8e Guo D, Huang H, Xu J, Jiang H, Liu H. Org. Lett. 2008; 10: 4513
8f Kaddouri H, Vicente V, Ouali A, Ouazzani F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 333
8g Larsson P, Correa A, Carril M, Norrby P, Bolm C. Angew. Chem. Int. Ed. 2009; 48: 5691
8h Swapna K, Kumar AV, Reddy VP, Rao KR. J. Org. Chem. 2009; 74: 7514
8i Murthy SN, Madhav B, Reddy VP, Nageswar YV. D. Adv. Synth. Catal. 2010; 352: 3241
8j Cano R, Ramon DJ, Yus M. J. Org. Chem. 2011; 76: 654
8k Yang K, Qiu Y, Li Z, Wang Z, Jiang S. J. Org. Chem. 2011; 76: 3151
8l Huang Z, Li F, Chen B, Xue F, Chen G, Yuan G. Appl. Catal., A 2011; 403: 104
8m Cristau H, Cellier PP, Spindler J, Taillefer M. Chem. Eur. J. 2004; 10: 5607

9a Finar IL, Godfrey KE. J. Chem. Soc. 1954; 2293
9b Guo C, Ren T, Wang J, Li C, Song J. J. Porphyrins Phthalocyanines 2005; 9: 430
9c Ju Y, Varma RS. J. Org. Chem. 2006; 71: 135

10 Patel HV, Vyas KA, Pandey SP, Tavares F, Fernandes PS. Synlett 1991; 483

11a Huisgen R, Gotthardt H, Grashey R. Chem. Ber. 1968; 101: 536
11b Huisgen R, Grashey R, Gotthardt H. Chem. Ber. 1968; 101: 829

12a Gonzalez-Nogal AM, Calle M, Cuadrado P, Valero R. Tetrahedron 2007; 63: 224
12b Browne DL, Vivat JF, Plant A, Gomez-Bengoa E, Harrity JP. A. J. Am. Chem. Soc. 2009; 131: 7762

13a Rai NS, Kalluraya B, Lingappa B, Shenoy S, Puranic VG. Eur. J. Med. Chem. 2008; 43: 1715
13b Asundaria ST, Patel NS, Patel KC. Org. Commun. 2010; 3: 30
13c Fang Y, Wu C, Larock RC, Shi F. J. Org. Chem. 2011; 76: 8840

14 Teo Y, Yong F, Lim GS. Tetrahedron Lett. 2011; 52: 7171
15 Cristau H, Cellier PP, Spindler J, Taillefer M. Eur. J. Org. Chem. 2004; 695

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